I have been busy on a few projects, most of which are wrapping up. Blogging has been light, but I have some fun things teed up in the near future.

I wanted to come out of hiding to share a few recent media mentions of “How Not to Invest,” along with a broader list of summer reading.

The 7 Best Investing Psychology Books from Next Book included HNTI, plus the latest work from my colleagues Ben Carlson (Risk & Reward) and Nick Magiulli (Just Keep Buying).  Along with those three, the top 7 list also includes Nudge by Nobel laureate Richard Thaler; Thinking in Bets by Annie Duke, Fooled by Randomness by Nassim Taleb and Trading in the Zone by Mark Douglas.

The other mention was from Jason Zweig of the WSJ. His Summer Reading List has a dozen books worth your time this summer.

In addition to “How Not to Invest,” it includes Robin Wigglesworth, A Fabulous Debt: The Epic Story of How Bonds Built the Modern World; Joseph Moore, How to Get Rich in American History; Morgan Housel,The Art of Spending Money and Alex Edmans, The Madness of Markets: Why Smart Investors Make Crazy Decisions and How to Exploit Them. 

A lot of good choices!  I have the Wigglesworth and Moore books on my desk, queued up for my hammock reading…

Sources:
Best Investing Psychology Books: 7 for Managing Your Own Behavior
NextBookList, July 19, 2026

A Summer Reading List
by Jason Zweig
Wall Street Journal, July 14, 2026

The post Summer Reading List appeared first on The Big Picture.

• What Americans Need to Understand About China: Ezra Klein interviews former Australian PM Kevin Rudd — one of the West’s most fluent China hands — on the gaps in American understanding that keep producing bad policy. (New York Times)

• Jony Ive is cooking in the OpenAI kitchen. “Perhaps a computer that makes you feel that you want to hug it is in order?” The former Apple design chief is now deeply embedded in OpenAI’s hardware ambitions. What happens when the man who designed the iPhone tries to design the AI device that replaces it? (Feed Me) but see Generative AI Is an Engineering Disaster: A shockingly inefficient trillion-dollar project. The Atlantic’s cover piece argues that generative AI isn’t just overhyped — it’s fundamentally unreliable as engineering, and the industry is in denial about it. The systems don’t work the way their makers claim they do. (The Atlantic)

• Two Million Workers Are Locked Out of an Improving Job Market: The share of job seekers out of work for six months or longer is hovering near highest level in five years. Share of job seekers out of work for six months or longer hovering near highest level in five years The headline numbers look better. But two million people — disproportionately older, less educated, or formerly incarcerated — aren’t benefiting from the recovery at all. (Wall Street Journal)

• Mapping the World’s Prices 2026: Which are the world’s cheapest and most expensive cities? Mapping the World’s Prices, now in its tenth edition, is the definitive guide to quality of life, rental costs and prices for phones, coffee, taxis and more in 69 cities from Abu Dhabi to Zurich. (Deutsche Bank Research Institute)

• JPMorgan is closing in on a $1 trillion market cap after posting record profits: The Wall Street giant’s market cap stood at about $935 billion. It would be the first bank to ever join the $1 trillion market cap club. Jamie Dimon’s bank is approaching a market cap that would have been unthinkable a decade ago. Record profits, dominant market position, and a stock price that reflects both. (Quartz) see also BlackRock Shares Rally After Assets Soar Past $15 Trillion The money manager’s stock rose 6.6%, powering the S&P 500 Financials to a record high (Wall Street Journal)

• Failing is Common, Trying is Rare: Putting in a mediocre effort at a given task is deeply irrational if our goal is success at that task. But often, when we put in a mediocre effort, it’s because we have other covert goals we’re not really acknowledging. The real bottleneck isn’t failure — it’s the unwillingness to attempt anything in the first place. Most people don’t fail; they never start. (Raptitude)

• What Would Jesus Design? A growing number of faith-forward interior designers are decorating homes Christ-first. Turns out it’s as good for business as it is for their souls. Architectural Digest visits the Christian interior-design movement. What would Jesus design? Apparently: lots of neutrals. (Architectural Digest)

• How Ukraine Brought the War to Russia: Long-range drone and missile strikes on Russian soil have shifted the balance of the conflict—will they be enough to end it? (The New Yorker) see also US military smartphones targeted through roaming and ad tech: Cyber attacks tried to track down American personnel in Middle East as Tehran attacked forces in the region. (Financial Times free)

• Researchers are uncovering ADHD’s links to these other health conditions: A growing body of evidence suggests that people with ADHD may be at risk for anxiety, disordered eating, migraines, long covid and other problems. The diagnosis turns out to travel with a surprising amount of company. A useful survey of the emerging comorbidity research. (Washington Post)

• There’s an Injury Epidemic in Pro Sports. There’s Also a Recovery Revolution. Athletes are pushing their bodies to astonishing feats, knowing that medical advances can heal them quickly.Pro sports has an injury epidemic and a recovery revolution running simultaneously. Bodies break faster; the science fixes them faster. (New York Times)

Video of the day: The Billy Joel Interview

Be sure to check out our Masters in Business next week with Jason Wenk, founder and CEO of Altruist, a modern custodian built as a clean sheet from the ground up, fully integrated with artificial intelligence. He began his career at Morgan Stanley before launching Retirement Wealth Advisors, and then FormulaFolios. The through-line of his career has been creating lower-cost, tech-enabled, financial advice.

Capital Markets Strategy. The AI Arms Race

Source: MUFG

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•  Developers Are In On The Joke: Apologize Later: Jonathan Miller on developers who build first and beg forgiveness after. The oldest play in real estate. NYC Development Legend Harry Macklowe’s Midnight Demolitions (Housing Notes)

• Why recruiters can’t find workers and new grads can’t find jobs (it’s not AI): The Post digs into why recruiters can’t find workers while new grads can’t find jobs — and no, it’s not AI. A hiring market full of broken signals. Experts say a major labor shortage looms because of population shifts and a mismatch between new graduates’ skills and employers’ needs. (Washington Post) But See Remote Work Leaves Younger Workers Sidelined. Youth unemployment has risen dramatically since the pandemic—as has the prevalence of remote work.The New York Fed’s research shows early-career workers are being disproportionately harmed by remote arrangements — less mentoring, fewer network connections, slower skill development. Analysis suggests that these trends are related, with remote work making it more difficult for managers to train and mentor new employees The people who need the office most are the ones least likely to be in it. (Liberty Street Economics)

• You should be glad your boss is so well paid: Because it probably means you’re being paid well too.  (FT Alphaville free)

• What Are the Chances of Your Prediction Being Right? I have a question for you. If you take all of the hearts from a standard deck of 52 playing cards, and then lay them out one by one, in how many different orders can the 13 cards be dealt? Joe Wiggins on the odds your market prediction is actually right — and why the honest answer should keep forecasters humble. (Behavioural Investment)

• Why the Bipartisan Housing Bill Can Still Become Law – Despite Trump’s Refusal to Sign: The 21st Century ROAD to Housing Act, which passed easily through both chambers of Congress in a rare display of bipartisanship, would ban large institutional investors from purchasing additional single-family homes. US News on why the bipartisan housing bill can still become law despite Trump’s refusal to sign. Procedural arcana, meet housing crisis. (US News)

• One of sci-fi’s most difficult questions about AI is becoming real: The rapid spread of chatbots and AI agents is intensifying a debate over who should be held responsible when something goes wrong. (Washington Post)

• How Putin Turned Japan Into a Den of Spies: Operating out of a Tokyo high-rise, a military intelligence unit finds the high-tech equipment that Russia needs to wage war. How Putin turned Japan into a den of spies: Russian intelligence quietly mining Japanese tech and industry for the war effort. (New York Times) see also Japan Is Building a New Intelligence Agency With Help From the West: Facing threats from Russia and China, Prime Minister Sanae Takaichi is breaking with World War II-era limits on security. Japan is standing up a real intelligence agency with Western help — a big deal for a country that’s been allergic to spycraft since 1945. (New York Times)

• Aspiring to Regional Domination, Iran Is Ready to Escalate Over Hormuz: New outbreak of fighting over the strait comes as Tehran sees itself as a winner in the war that would establish a new Pax Iranica in the Middle East. Iran isn’t bluffing on the Strait. The Wall Street Journal reports on Tehran’s military posture and its willingness to escalate — with global energy markets as collateral. = (Wall Street Journal)

• The 35-year-old powering Paul McCartney and the Rolling Stones: Andrew Watt listened obsessively to rock as a teenager. Now, he considers all of his heroes — from Elton John to Mick Jagger — to be friends. Meet Andrew Watt, the 35-year-old producer powering late-career McCartney and the Stones. The Post profiles rock’s favorite whisperer. Andrew Watt listened obsessively to rock as a teenager. Now, he considers all of his heroes — from Elton John to Mick Jagger — to be friends. (Washington Post)

• Norway turn World Cup heartbreak into celebration as huge crowds pack Oslo: Norway loses the World Cup final and Oslo throws a party anyway. Huge crowds, zero bitterness — imagine that. More than 100,000 fans flooded the streets of Oslo, Norway’s capital, to give their team a warm welcome, turning the heartbreak of their World Cup exit into ⁠a massive national celebration. (The Guardian) see also Why is tiny Norway so good at sports? It’s more than Erling Haaland.  A youth system built on joy and participation instead of early specialization. One answer is that, from the youngest ages, Norway thinks about sports in a radically different way. In Norway, teams do not keep score before children turn 11, and the players cannot be separated into ranks until they are 12 or 13. Sports begin not as a race to the top, but as a constitutionally guaranteed social benefit for all, a place to learn, grow, and – perhaps most importantly – have fun. (Christian Science Monitor)

Video of the day: Why Tesla Sales are Falling Short in the U.S.

Be sure to check out our Masters in Business interview this weekend with McKeel Hagerty, CEO and Chairman of Hagerty. We discuss how he transformed the family boat insurance business into a “sexy” driver-forward business. We also discuss our love of collectable cars and his love of his first car, a Porsche, that he bought at the age of 13.

How many Americans are using AI — and how?

Source: USA Facts

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The transcript from this week’s, MiB: McKeel Hagerty, CEO and Chairman of Hagerty , is below.

You can stream and download our full conversation, including any podcast extras, on Apple Podcasts, Spotify, YouTube (video), YouTube (audio), and Bloomberg. All of our earlier podcasts on your favorite pod hosts can be found here.

~~~

Masters in Business: McKeel Hagerty, CEO & Chairman, Hagerty

Barry Ritholtz (00:00:08): This week on the podcast, another extra special guest. McKeel Hagerty is chairman and CEO of Hagerty specialty insurance. Fascinating company. They took a little niche wooden boat insurer and turned it into a publicly traded company by embracing the community around collector cars, trucks, boats, et cetera. I thought this conversation was really quite fascinating, not just as a car guy, but as a business guy. And I think you will also. With no further ado, my conversation with Hagerty’s McKeel Hagerty.

McKeel Hagerty, welcome to Bloomberg.

McKeel Hagerty (00:00:56): Thanks for having me.

Barry Ritholtz (00:00:58): So let’s start with your background. You get a BA in English and philosophy from Pepperdine, and then you get a master’s in theology at St. Vladimir’s Orthodox Theological Seminary. What was the plan — to become a priest?

McKeel Hagerty (00:01:14): I think about my academic career in a couple of phases. I was an entrepreneur from the time I was young — I had a bunch of businesses when I was very young — and thought I would go study business in college. And I ended up falling in love with philosophy and literature and all these things; I was a philosophy and English major. I was a good student and I thought I’d get my PhD, but I needed a little break to work on languages and some things. And I learned about St. Vladimir’s, which is just north of New York here — it’s up near Rye or Scarsdale. And it was this incredible experience, because I got to work on my languages. I learned a lot about leadership, actually, at the seminary, because there are some pretty extraordinary individuals there. And there is no doubt about it — you are there to study to become a priest. And while that was not my driving reason to go there, it’s a little bit like Michael Corleone — they kind of drag you in, and before you know it, you’re suddenly thinking about becoming a priest.

I didn’t become a priest, because then I moved on and started my doctoral work in philosophy up in Boston, and did not complete that because the family business called. I had worked in it during the summers up until then, with mom and dad and my two sisters. And all of a sudden I found myself no longer thinking about exams and a dissertation and all those things, and thinking about this really cool business.

Barry Ritholtz (00:02:44): So let’s talk about this business. The hagiography is: your parents, Frank and Louise, started Hagerty Insurance Agency in Traverse City, Michigan (Yes.) for what I never would have guessed was an actual business — collector wooden boats. (That’s right.) Are there enough collector wooden boats to sustain a full business?

McKeel Hagerty (00:03:07): There are enough wooden boats to insure to sustain a very small family business, with a few employees. It was kind of a retirement gig for my mom and dad. They had had a general insurance agency, and they sold that, and they wanted something else to do. But there were a couple of principles in the back of their mind: they wanted a national business instead of a local one. They wanted one that was in a niche, rather than sort of general purpose. And they wanted one that could have real sustainability over a long period of time. So wooden boats was an unoccupied business space — a literally unmet need. They matched the unmet need with an underlying interest in wooden boats and in cars — my dad was a wooden boat, vintage boat guy and also a car guy. And so this was just the fun of combining the business knowledge with a passion. And again, my sisters and I all kind of helped out when it was much smaller, and we kind of stumbled into the car insurance business, which was much, much larger than the wooden boat business.

Barry Ritholtz (00:04:10): Even the collector car business is orders of magnitude —

McKeel Hagerty (00:04:13): Oh, orders of magnitude larger. Millions of vehicles.

Barry Ritholtz (00:04:15): But let’s not jump quite that far ahead. You and your dad used to work on cars — rebuilding projects. You mentioned you had a couple of side hustles: lawn mowing, things like that.

McKeel Hagerty (00:04:29): Yeah, my apple orchard.

Barry Ritholtz (00:04:30): You spent 500 bucks buying a 1967 Porsche 911S when you were 13. (Yes.) I wouldn’t be allowed to buy a car at 13 — I was lucky I had a bike. And then you and your father rebuild this.

McKeel Hagerty (00:04:46): That’s right. I will also note it was the only really good car deal I’ve ever done in my life, so just for what it’s worth.

Barry Ritholtz (00:04:52): So I’m going to assume that was the spark that started your enthusiasm for cars.

McKeel Hagerty (00:04:58): Yeah, it was. And you know, my dad was a do-it-yourselfer, hobbyist, restorer guy in the garage. And both my sisters also restored cars with him — they were older than I was. And then I was the third along, and we convinced this older gentleman in our town to sell us this 911S for 500 bucks. And I had to mow an awful lot more lawns and sell a lot more apples out of my orchard to buy the parts to restore the car. But by the time I could drive, it was ready.

Barry Ritholtz (00:05:27): Good planning.

McKeel Hagerty (00:05:27): It was great planning. And I can tell you, there was nobody in my high school driving a Porsche, so I would sneak it into the teachers’ parking lot, because no one would believe that a student had a Porsche. (That’s hilarious.) But back then, in the eighties, cars like that were not expensive. They were not considered to be necessarily that valuable. They were just kind of cool older cars. And so we kind of approached it as a family — like, hey, you can get a lot of car for not a lot of money, and you can have something really fun to enjoy. And so that was just my life growing up.

Barry Ritholtz (00:05:59): I love that. The 300 SLs from the fifties were being sold at a depreciated price in the sixties and seventies. (Oh, of course.) It’s astonishing.

McKeel Hagerty (00:06:07): Well, the most valuable car today, people will tell you, is the Ferrari GTO — 1962. They’re worth tens and tens of millions of dollars. But in the 1970s, you could buy them for 15 grand. They were nothing. And now they’re 50 million, 60 million dollars.

Barry Ritholtz (00:06:22): Unbelievable. That 911S you restored — still have it?

McKeel Hagerty (00:06:27): Still have it.

Barry Ritholtz (00:06:27): Still drive it?

McKeel Hagerty (00:06:28): Of course. It’s my first car out every season and the last one I put away.

Barry Ritholtz (00:06:32): Wow, that’s amazing. We could spend a lot of time talking about what else you drive, and we’ll get to that later. I’m curious — when did you first realize Hagerty could become something a whole lot larger than a niche wooden boat insurer?

McKeel Hagerty (00:06:50): Oh, we had already started the car business in the early 1990s. I’ve had a couple of aha moments, and this one — I remember it like we were sitting here today. It was the fall of 1995. I was doing my doctoral work in Boston, and we were reading Plato’s Republic in Greek. So I’m up at Boston College, we’re working on Plato’s Republic in Greek — that’s a big slog, I can tell you. And I was trying to help out the family business kind of from a distance.

And the challenge with insurance — insurance is an incredible industry. It’s stable. There’s a lot more interesting stuff to it than people think. But it is just not very sexy to talk about. Nobody loves talking about insurance. And even with these big brands and stuff today, they still don’t want to talk about it very much. And so I was literally sitting in this Plato’s Republic class, and on the side of my notebook I wrote this thing: if we would just stop acting like an insurance business and start acting more like a club for car owners, it would just transform the conversation that you’re having with people — because then you’re acting more like a car person, instead of an insurance person trying to sell a car person something. And I literally wrote this idea of: turn Hagerty into a car club. I wrote it in my notebook, and I closed my notebook. I went home that night to my apartment, and I dropped out of my PhD program right then and there, and I went home the next week.

Barry Ritholtz (00:08:12): Well, let me validate that — not that you, as a public company, need my validation. Full disclosure: I have a few of my cars insured with Hagerty. I’m a member of the club. I get the Driver’s Club magazine. But it’s obvious in hindsight — oh, of course you’re going to focus on this niche that is kind of ignored (Yes.) by the major insurance companies. How challenging was it to convince the rest of the family — hey, this is the way to go; we are not an insurance company selling to car collectors, we’re car people checking a few of their boxes?

McKeel Hagerty (00:08:53): It took me a few years. You know, we were a very close family. It was really fun to work together with everybody in those early days. My dad retired in kind of that late nineties; my mom retired shortly thereafter. I was working with my sisters. So they gave me enough rope to go test it out — that if we just changed the dialogue and acted like we’re going to build an automotive branded business that happens to sell insurance, and we’re going to do it around this membership concept.

It wasn’t like no one had ever done something like that. If you think in the early days, AAA was kind of like that — the motor club (they’re very different than that now). Or if you were to even think of something like AARP, which is a different sort of segment — they sell a lot of insurance and they treat this group of people well. USAA, serving military families. It’s just, nobody had ever done it in a business like ours. And so it took a little while to convince them that that was the way to go to market, and that we could change the way we were thinking.

But you mentioned something — there was another piece in this, which was the next aha. And the next aha was that most of these cars were insured by the big insurance companies. So think State Farm, Allstate — today, Progressive, Geico, everybody. And we’re a little company. I mean, we had a tiny family business. How the heck are you going to compete against these monsters? And so after we got the club up and running, I realized — well, what if we just partnered with these companies rather than competing against them, and said: look, we are going to do one thing and one thing only. We’re going to be expert in these cars. We know the customers really well. We’re building a really big, rich bunch of data. What if we partnered with them? And so the first big partnership like this, we landed 22, 23 years ago, and that was with Allstate. And Allstate’s huge — again, huge company. I knew they insured hundreds of thousands of these cars.

Barry Ritholtz (00:10:50): Spun out from Sears so long ago.

McKeel Hagerty (00:10:51): Exactly. Lots of interesting things in that company. And I met the CEO at the time, through people who helped connect us. And I said, look, I think I can make you better at this one tiny little thing if you just give us a chance. And they’re still a partner today — that program still grows every year. And now we’ve just moved through the entire insurance industry. We’ve partnered with virtually all of the big insurance companies. And so today, if you insure your home and your auto and everything with one of them, but you have a vintage car, collector car, whatever you want to call it, that usually comes to us. And so the big scalability of the business was: one, show up like a club, this member organization; and two, partner rather than compete. Because if you’re small, it’s impossible to compete against a huge company. But if you partner with them, it changes the game.

Barry Ritholtz (00:11:45): Well, when you say it’s impossible to compete — one of the fascinating things about insuring an old ‘Vette or an old Porsche is, any of the big firms are going to charge you 1,500, 2,500 a year. Alright, so I have a ’67 ‘Vette, which is actually my least favorite car to drive.

McKeel Hagerty (00:12:08): I’ve got to ask — which motor?

Barry Ritholtz (00:12:10): The 327. Yeah, but with a stick. Nassau blue over white. (Very nice. Spectacular.) But it’s a pig to drive. But it doesn’t matter, because I think Progressive was like 2,200 — you guys were 500 and change. Because of the data: you guys know how often these are driven, know the value, know they’re really not going to get stolen. (That’s right.) As much as Gone in 60 Seconds made it look sexy, everybody knows these cars, their VINs, where they are — especially something rare and valuable, which the ‘Vette is not. It’s really fascinating that nobody else saw this until you guys did. How did the pricing model come along?

McKeel Hagerty (00:12:58): Well, you talked about how you drive your car, but you probably don’t drive it very much. You probably have daily drivers that you drive more, and you are less concerned about where you park them and that sort of thing. My late mother passed away just two years ago. I remember asking her every year — her memory wasn’t so great towards the end of her life — like, Mom, what made this business special? And she would just say: because people take good care of their toys. (Of course.) And that is the core emotional nugget of this business. People have a toy, they spent real money on it, and they take good care of it. And wherever there is care, there is better insurance risk. So you can charge less. You can build marketing around that. You can get a little bit of momentum.

Barry Ritholtz (00:13:41): But not just a little less. It’s not like you’re beating them by 10%. It’s a fraction of what you pay for regular insurance.

McKeel Hagerty (00:13:48): Well, right. And look, the typical ’67 Corvette owner probably drives that car a thousand, maybe 1,500 miles a year. Some years less.

Barry Ritholtz (00:13:56): Half the guys in my car group — and they’re almost all guys, but not exclusively — some of these guys have 10, 20, 30 cars.

McKeel Hagerty (00:14:07): Exactly.

Barry Ritholtz (00:14:07): So if they’re driving a car, it’s something different. Maybe they’re putting 500 miles a year on each car, at most.

McKeel Hagerty (00:14:16): So, one of the things you asked about — pricing. Not only is the pricing on the physical car less expensive with us; the liability is too. And it’s exactly to that point: you can only drive one car at a time. Liability follows the person, not the car. And so we had an ad very early on in the program — there was a now-late collector out in the Pacific Northwest with over 2,000 cars. We put his name and face on one of our ads, and it said: here’s Harold LeMay, our worst nightmare, because he has 2,000 cars, but we charge him only one time for liability.

Barry Ritholtz (00:14:50): So how do you — is that a fleet insurance? How do you do something —

McKeel Hagerty (00:14:52): Kind of like that, yeah.

Barry Ritholtz (00:14:53): If someone has more — and I think the line I heard about tattoos applies to cars: two tattoos is either too few or too many. And if you have half a dozen or a dozen cars, it’s probably too many to manage yourself, but too few to hire a full-time Jay Leno-like guy to run it. (That’s right.)

McKeel Hagerty (00:15:15): Most people are space limited. If they have enough money to be into it, they end up buying everything that they can afford and still store.

Barry Ritholtz (00:15:24): The storage is the problem. I’m waiting for permission to build a garage. (There you go.) A detached garage, as opposed to my built-in garage. And if that gets approved by the town, that’s going to be both dangerous and expensive.

McKeel Hagerty (00:15:39): Well, I’m going to love it though, because then I’ll have more to insure for you.

Barry Ritholtz (00:15:41): That’s six more cars’ storage for you guys. Yes. Really, really interesting.

Coming up, we continue our conversation with McKeel Hagerty, CEO of the specialty insurance firm, talking about how he built the company into a one-and-a-half-billion-dollar revenue driver. I’m Barry Ritholtz. You’re listening to Masters in Business on Bloomberg Radio.

Barry Ritholtz (00:16:10): I’m Barry Ritholtz. You’re listening to Masters in Business on Bloomberg Radio. My extra special guest this week is McKeel Hagerty. He is the chairman and CEO of Hagerty collector car insurance. The firm insures every collectible vehicle — and a handful of boats — for almost 3 million collectors. So: 2025 revenues of 1.5 billion. 1.3 billion in written premium — a record. 371,000 new members. Net income plus 91%. This is a real publicly traded company — HGTY. (Yes.) Wow.

McKeel Hagerty (00:16:49): I used to have hair when we started all of that. But, you know, things are going well.

Barry Ritholtz (00:16:53): So I guess if you’re not pulling your hair out of your head, you’re not public. Let’s talk about how you’ve driven this. One of the interesting insights that seems to have shaped your strategy was that collector cars aren’t just financial assets — they’re emotional assets. You described them as favorite toys. How did that shape how the firm developed?

McKeel Hagerty (00:17:20): Well, we started in the simplest possible way, which was as an insurance agency — you might have mentioned that in the first intro, and that’s true. That’s the easiest way to get into one of these things. As I mentioned, we started with kind of a specialty product, which was insuring special cars. The insurance policy forms were unique; our pricing — we had a unique approach. We had this Driver’s Club model that started really helping that compounding aspect of it. But one of the big pieces that I guess I dreamed of is that if we actually started taking real risk and became the insurance company itself — not just an agency selling policies for somebody else — it would be the same customer coming in, but we’d have so much more of a chance to really build revenue behind it.

So the other big piece — my first aha was the Driver’s Club; the second aha was really realizing we needed to partner rather than compete with the big insurance companies — was: how do we start taking risk? That’s been a multi-year, really decade-long journey that we started in 2017, got up and running, and it was really a big key piece of how we went public in 2021. Everybody knew we had a unique angle on this market, that our economics looked great in the business, but that we could realize even that much more. And so that’s really been the next big piece of all of this. And it all kind of compounds on itself, because if you insure a car, we use the club to kind of engage people. You mentioned reading the Hagerty Driver’s Club magazine — by the way, I don’t think the word insurance is mentioned in that magazine anywhere.

Barry Ritholtz (00:19:06): Not at all. It’s cars and roads, really.

McKeel Hagerty (00:19:07): Yes. And it is now the highest-circulation car magazine in the world. (No kidding.) It is. Yeah.

Barry Ritholtz (00:19:13): I did not know that. That’s really interesting. So the evolution from insurance to an automotive lifestyle brand goes beyond the club membership, goes beyond the magazine — events, auctions, valuation data. Walk us through how that all evolved.

McKeel Hagerty (00:19:33): Yeah — I was a big fan of car magazines, a big fan of automotive media. I mean, that’s how I read my way into understanding the car world, and going to events. And I always remember somebody told me once that if you’re going to go into a niche business that you’re really proud of, you kind of need to have the high ground on your side. And for me, the high ground was, if I could have a media property where we would kind of have that intellectual high ground, that would help.

The other piece is the data aspect of it. When I was growing the business and the team — you know, we have incredible teams — we’re out there trying to figure it out. Valuing these cars was so tricky, because there were a lot of opinions about what cars were worth, but not a lot of really good data. And so as we were investing in the media pieces — talking about cars and entertaining people — we built the data resources. We call it our Automotive Intelligence group. We have by far the richest sets of data about how to value these things, and it’s down to that VIN or serial number.

You mentioned — well, how does a big insurance company… why didn’t they do it? I remember this conversation years ago, in one of those partner discussions, where the CEO was a car guy, really wanted to kind of compete with us, wasn’t sure if he wanted to partner with us. And I said, well, do you know what a 1969 Camaro is? And he said, I sure do — he was pretty happy with himself. And I said, you may not know that in 1969, the Camaro came in 147 different variants. (Wow.) And that year, the least expensive one was worth about 11 grand, and the most valuable one was worth about 1.1 million. And you can’t tell the difference by looking at them from the outside. You have to understand what that serial number is. And I said: we built a patented serial number decoder for all cars pre-1981, so that we could understand our universe and start providing that data. And that’s why our partners like us.

But it’s a real asset to have that kind of data, and then build on it every year. You mentioned 371,000 new customers — we’ll do quite a bit more than that in 2026. Those are all — it’s not just insurance revenue, it’s also data coming our way. What are people buying? What are they insuring them for? What do they sell? When somebody sells a car, it’s also a data point. And so for us, that data piece — and it’s all a big… not just because I’m a car person — I view it as a flywheel. It all kind of spins, and insurance is a beautiful thing, but the rest of it speeds up the flywheel.

Barry Ritholtz (00:22:01): Yeah, to say the very least. So the valuation tools you have are really interesting. The Bull Market List you have has become very influential. I actually reference some of your valuation tools in a chapter of my book, on selection bias. Every time some car goes for a new record high, there’s always a bunch of media coverage, and they talk about — look at what a great investment this is. And it’s like, no, that’s all survivorship bias. Show me the other 10. Don’t show me what was the best car of the past 50 years — what car are you going to buy now to put away for the next 50 years? (Yes.) That’s a much harder question, because you don’t know the answer. But your valuation tools have been really helpful, that sort of stuff. How did you build that capability? Is it simply just — hey, every data point we come across from clients, we’re going to suck into a database and figure out?

McKeel Hagerty (00:22:57): That was exactly it. I mean, most media outlets that weren’t part of our world — if they were covering the space, they were using a lot of anecdotal information, kind of dealer-fed information, or just looking at public auctions. And I love public auctions too — you can learn a lot from watching what all the different auction companies do. And now, with so many good online places, it’s even more data. But what we realized, with our scale, is we just had way more data points than all of that. Because again — people buying cars, insuring them with us, adding, deleting — it was just this big flow. And yeah, it took a lot of people a lot smarter than I am to build not just the database stuff, but the analytics capability around it. And now, with AI, it’s even better. And then, as we started realizing we could get other data sources that help us validate even more — not just in the US, but outside of the US — it’s really been a fun part of the business. I’ll tell you what — it’s a smart team, and I love learning from them. They teach me stuff every day that I need to know.

Barry Ritholtz (00:24:00): You mentioned auctions and online auctions. In addition to Bring a Trailer and Cars & Bids and PCARMARKET, you guys are now going to get into online auctions for your clients’ cars? Or are you just partnering with someone?

McKeel Hagerty (00:24:16): Oh, no, no. We have our own — the Hagerty Marketplace platform, which is online auctions. And then also now —

Barry Ritholtz (00:24:24): You’ve had online classifieds for a long time. (Yes.) How rapidly is the auction side growing?

McKeel Hagerty (00:24:29): It’s growing rapidly now. We have such a supply — we have way more supply than you think. And if you think about some of those other great companies — Bring a Trailer has been such a darling in this space; Cars & Bids, the number two in the US — there’s a supply and demand balance that everybody has to strike. Because if you flood a digital marketplace with too much supply, then the bidders go away. And if the bidders go away, then nobody’s happy — people won’t put their cars on it. So it’s a fast build, but it’s steady.

The live auction side of the business — Broad Arrow, which was an acquisition we did after going public — that’s a remarkable business, because I had followed that industry for a long time around the world. But it’s all about getting the right team. And in my mind — because I’m very protective of our brand and our reputation — we had to have the kind of team that wasn’t just prepared to build the number one live auction business; they have to do it in a way that I’m proud of. Because things will go wrong. You have to make things right for customers. Sometimes cars that people bring to you to sell aren’t described exactly as they actually are, and you have to find that out and politely tell them — well, I’m not sure this is a million-dollar car; it’s a hundred-thousand-dollar car. And sorry — if you want us to sell it for a hundred thousand, we will, but we’re not selling it for a million. Because it’s our reputation too.

And so the way I think about it now is: most people come to us to insure a car. Then they buy the membership thing, and we engage them and do media and a lot of fun stuff, invite them to our events. And about every seven years, on average, somebody buys or sells a car. And that’s where I want to be there and present in their minds, so that we help them on that transactional side. Plus, you’ve probably been to auctions or watched them on television. (Sure.) They’re fun. Car auctions are super fun. It’s live, it’s vibrant, it’s interesting. Sometimes there are multimillion-dollar cars up there selling, where you can’t even believe anybody would pay multimillion dollars for this car. And we do that too — that’s why we have Broad Arrow. We connected it with some of our concours events — in many cases, around the world. We just had our Broad Arrow auction at the Villa d’Este concours, the Concorso d’Eleganza. And that was a really successful sale, and a super cool place to have an auction — right on Lake Como. (Yeah.) In Italy.

Barry Ritholtz (00:27:01): Looked beautiful. You’ve been a judge at Pebble Beach for a while, I know.

McKeel Hagerty (00:27:08): 25 years — I think this is my 25th year.

Barry Ritholtz (00:27:09): Wow. And I know there was an affiliation with one of the local concourses here. Maybe it’s Greenwich?

McKeel Hagerty (00:27:14): Greenwich, yeah. That is an event we own. So we produced that just recently.

Barry Ritholtz (00:27:19): That’s — it’s too close to a holiday weekend, otherwise I would be there.

McKeel Hagerty (00:27:24): Oh, you’ve got to come.

Barry Ritholtz (00:27:25): I’m usually out at the beach on Memorial Day weekend. But we’ll circle back to that. I’m also a big fan of your YouTube channel. I really like Jason Cammisa’s work. I’ve learned a lot about cars that I think I know — and then he does a deep dive into a particular model, and I’m like, I didn’t know that about the Toyota Supra. Who would’ve guessed? How did YouTube become such a major part of your brand?

McKeel Hagerty (00:27:54): Well, it’s really the de facto platform for people watching kind of introductory-level automotive content, and obviously lots of brands are putting stuff out there. But what we realized — if you think about the big arc of how people have learned about or consumed automotive media, where it’s shifted since the nineties: magazines were the main platform for a long time. Then you got the first dedicated cable networks — Speed, Speedvision, AutoWeek — you started seeing auctions on there. But then a lot of that content started migrating to YouTube. What I wanted to do was do it at the same high quality we were doing in the magazine. So hire total pros, shoot the stuff really well — great cameras, great locations, all of that.

Barry Ritholtz (00:28:48): It is obvious high production value. There are a lot of YouTube channels that are kind of interesting, cars or otherwise, but the appeal has always been: two iPhones, a wireless mic, and a GoPro — you could cobble something together. I’ve seen a bunch of channels that are using these. You guys really put a lot of thought and a lot of time, effort, and money into it.

McKeel Hagerty (00:29:19): Well, we do. And they’re not all just drag races — nothing wrong with drag races; I like them too. It’s a kind of data point about what makes a car cool. But I think Jason just takes it to a whole new level. We also have — by the way, we have a FAST channel on Samsung TV, on Amazon Prime; our content is available out there like a digital television show. Our Barn Find Hunter show, for years — you’ve probably seen it — which is this incredible talent, Tom Cotter, going around and finding great cars in barns and kind of doing the big reveal. Like an Antiques Roadshow kind of concept, but in the garage, rather than brought to some studio somewhere. And people like it. There’s some interesting fascination with the US television audience of finding the treasure in the garage — and don’t you wish it was you who found it? I find them fascinating.

You may have even seen one of the shows we produced for a long time — they’re kind of winding down — called Redline Rebuild. (Yep.) It was where we would do these time-lapse rebuildings of an engine, where you take a big dirty engine apart, and it would all kind of appear to assemble itself on an engine stand, and then it would start. It was just mesmerizing.

Barry Ritholtz (00:30:34): That’s the word I was about to say.

McKeel Hagerty (00:30:36): Just mesmerizing. Yes.

Barry Ritholtz (00:30:37): There’s another channel that does the same thing with old watches (Oh wow, interesting.) and rebuilds them. And it’s the same sort of — why is this so fascinating? It’s the exact same thing as Redline.

Coming up, we continue our conversation with McKeel Hagerty, CEO and chairman of Hagerty specialty insurance, discussing the collector car community today. I’m Barry Ritholtz. You’re listening to Masters in Business on Bloomberg Radio.

Barry Ritholtz (00:31:11): I’m Barry Ritholtz. You are listening to Masters in Business on Bloomberg Radio. My extra special guest today is McKeel Hagerty. He is the CEO and chairman of the namesake specialty insurance company specializing in collectible cars — automotive everything, from cars, trucks, military vehicles — including classic wooden boats. Are those all Chris-Crafts, or are there some other brands that make their way through that?

McKeel Hagerty (00:31:35): Well, Chris-Craft and Century were the two big manufacturers in the United States. There were sort of some more boutique brands, like Gar Wood and Hacker-Craft, which were really high end.

Barry Ritholtz (00:31:46): I’ve been in a Hacker-Craft. Those are big — they tend to be a little bigger.

McKeel Hagerty (00:31:49): Right, a little bit bigger — triple-cockpit kind of style boats. And for those who are really into the artisanal cheese of the boat world — the Canadian brands. There was a whole group of really fine boat builders up there: Minett-Shields, Ditchburn, Greavette — brands that most Americans would not know of. But if you ever get a chance to go up to the Muskoka Lakes, which is just north of Toronto, they’re just exquisite, beautifully built boats. They’re considered like national treasures up there. So you don’t see many of them in the US. But that was part of my upbringing. When my mom and dad were building the boat business and I was a teenager, it was like — huh, we’re going to a boat show, going to Canada, going to Lake Tahoe, going to the Finger Lakes of New York.

Barry Ritholtz (00:32:37): That’s so interesting. I took some friends to the boat show last year, and the new Chris-Crafts are shockingly beautiful. (Oh yes.) They have aged into modernity really well. It’s almost like a retro-mod, because it’s very contemporary and very modern, but clearly the design language from way back when.

McKeel Hagerty (00:33:02): I think it’s a little bit like that Hinckley crowd (Yes.), where they’re trying to find a retro-modern boat, but with kind of retro looks.

Barry Ritholtz (00:33:10): And I love it. So let’s keep this on cars, away from boats. There’s a quote of yours that I have to start with, because I really like it: “The best piece of advice is to buy the car you want to drive, and then buy the best example you can afford. This may sound obvious, but not all vintage cars drive the way people hope they would.” There’s nothing in that I disagree with. Discuss.

McKeel Hagerty (00:33:41): Yeah. I think there are so many people that envision — someday, when they have that little bit of extra resources — you know, that’s going to be my toy; I want to get into the car world. And if they weren’t a hundred percent in this their whole life, or their parents weren’t into it, or you didn’t have an uncle or somebody in your life who let you drive in these things, I often recommend people try to get a chance to drive what you think you want. Because the older cars do drive very differently. (Yes.) And even if you think of, say, muscle cars from the sixties — they were very fast. I mean, these are cars that are —

Barry Ritholtz (00:34:14): In a straight line.

McKeel Hagerty (00:34:15): In a straight line — a lot of power. They do not stop or turn as well as you think, and you just have to get used to that. I mean, I love cars of all generations. I love driving very early cars; I have some newer cars. And I always just have to kind of center myself when I get behind the wheel, to remember — okay, this is not my Porsche Taycan, which is this incredible piece of technology, an electric car. It’s a vintage internal-combustion car with funky brakes, and you have to be ready for it. So I always recommend people drive them. And recognize that maybe it had air conditioning, maybe the air conditioning doesn’t work — it doesn’t matter. Roll down the window and just enjoy yourself.

Barry Ritholtz (00:35:00): Manually —

McKeel Hagerty (00:35:01): Manually roll down the window.

Barry Ritholtz (00:35:02): I tell the story — the ‘Vette, the ’67: it’s a lap belt, not a three-point belt. They couldn’t be bothered to put a passenger-side mirror on, because, you know, what are you even going to see? And the steering is just beastly. But I also like the concept of buy the best example you can afford. And I find myself constantly saying to people: a cheap Aston Martin is the most expensive car you could possibly buy. (Yeah.) But people don’t really get that.

McKeel Hagerty (00:35:35): Yeah. And look — different areas of cars come with their own challenges sometimes. As we’re seeing this onslaught of new generations coming in and wanting to buy slightly newer cars — I mean, it’s 60-whatever percent of all of our new quotes and new cars coming into the space are all relatively newer cars: 1980s, nineties, two-thousands cars. Some of those cars, for example — it may not be a mechanical issue that can drive you a little crazy; it’s an electrical issue that’ll drive you a little crazy. If you think of some of the screens and the CD players and all the little control things that, back in 1990-whatever, were the biggest whiz-bang feature — well, it doesn’t work so well anymore. The car runs fine, but you’re not going to be able to use the antiquated nav system. I just tell people: relax, it’s fine. Enjoy the car, drive it. All my kids always ask — well, does the radio work in this thing? I’m like, I have no idea. It’s never been on. I’m there to drive. And it’s such a fun activity, as you know, to go and just enjoy driving a car for pleasure.

And the first thing I tell people who are sort of new to the space — they say, well, I want to take it out to dinner. And I’m like, make sure you take it out during the day first a few times, because sometimes cars leave you in the restaurant parking lot at night. So people always ask, why don’t you drive them at night? And I’m like — because I’m not sure I’m going to get home.

Barry Ritholtz (00:37:06): If you’re used to modern cars, you will be shocked at how terrible the headlights are — on, forget sixties, even eighties-era cars. Those were not really great headlights.

McKeel Hagerty (00:37:19): They weren’t great. They’re not dangerous or anything. You just have to be aware (Right.) that they don’t have all the modern technology.

Barry Ritholtz (00:37:24): When all the headlights were that way, you just said, this is what the lighting is, and you had to be aware of it. (That’s right.) It’s when you go backwards, you take a lot of things for granted — forget the blind-spot warnings and the backup cameras, just your expectation of field of vision (Yes.) is so different.

McKeel Hagerty (00:37:43): It’s a different kind of attention, driving a vintage car.

Barry Ritholtz (00:37:47): It’s much more focused.

McKeel Hagerty (00:37:48): It’s more focused. And I love it. And I encourage people — just try it out. It’s a great experience.

Barry Ritholtz (00:37:55): So what are some of the bigger trends you’re seeing in collecting? What’s changing these days?

McKeel Hagerty (00:38:02): Well, again, big story — contrary to data that we were reading a few years ago, the next generations are absolutely into cars. They like them. They’re just into different kinds of cars than our parents were, or we were.

Barry Ritholtz (00:38:13): Well, doesn’t every generation sort of lust after the cars from the high school parking lot?

McKeel Hagerty (00:38:19): I think that’s right. And they’re different. One of my little cottage industry things that I do: if I’m ever driving anywhere near a high school parking lot, I look to see where the young car people park their cars. And they usually park them in the back of the parking lot, not up near the school, and they all park next to each other, so they can go hang out afterwards. And what you’re going to see right now, with the 17- and 18-year-old car people in these high schools: you’re going to see BMWs, you’re going to see Audis, you’re going to see various performance Japanese cars. You’re not going to see anything fancy — they can’t afford them. But those are the cars they’re starting with.

Trucks are, of course, another big entry point, and it’s been another huge trend. So not just pickup trucks, but kind of vintage SUVs. So Jeeps are still, right now, one of the hottest brands — it’s huge. Broncos are one of the hottest things, of course, if they can afford them. A Land Rover, or International Scouts — these are the cars that people are interested in, because so many cars today are SUVs anyway, and the vintage versions of them are these kind of more off-road vehicles. And there’s a big industry of modifying them, making them work a little bit better. So that’s another big trend — next generation, trucks, I guess I would say.

And flying over the top of the whole industry, at the top end of the market — just to add on to the answer to your question — the ultra-luxury, kind of supercar manufacturers are making more cars than ever before. And so you think of those brands — like Ferrari or Lamborghini or Bentley, or even Porsche, my beloved 911s — those companies are just building a lot more cars and pumping them out into the market, at price points that are different than they used to be. When Ferrari or Lamborghini were building hundreds of cars a year — well, now Ferrari is a 14,000-unit-a-year manufacturer. Lamborghini, when you add their SUV in, is an eight or nine thousand vehicle manufacturer. I mean, when I was a kid, you never saw a Lamborghini unless you just happened to be in Beverly Hills or Palm Beach or something. And now they’re everywhere. I mean, even in my little town in northern Michigan, there are a couple of Lamborghinis driving around. I’m like, oh my goodness. That’s amazing.

Barry Ritholtz (00:40:34): What’s crazy is, where I live, I am 15 minutes from a Ferrari dealer, two Porsche dealers, the Bentley-Lamborghini dealer. And I take it for granted — I see these cars all the time. But as a kid, you hardly ever saw these around. A Porsche was an exciting thing.

McKeel Hagerty (00:40:54): It was. So they are building my next generation of customers. Every one of these manufacturers is like my best friend, because they’re building the cars that I will be insuring this year — and 25 years from now.

Barry Ritholtz (00:41:07): So your boy Jason Cammisa mentioned he’s only a manual driver. I embrace that — makes the car even that much more difficult to steal. But I’m curious — amongst the trends in collecting, I’ve been hearing about a move towards analog, towards manual, away from the big dominant screens. What does your data say?

McKeel Hagerty (00:41:33): Well, it’s true. And in fact, you think about some of those very same supercar manufacturers that signaled years ago — we’re getting rid of manuals; everything’s going to become this super electronic sort of driving experience —

Barry Ritholtz (00:41:46): Faster on a track. Faster on a track.

McKeel Hagerty (00:41:48): Yeah. And they are. And by the way, the one nice thing about the PDK — if you drive them in the winter… I happen to love driving Porsches in the winter. PDK is pretty nice in the snow, for what it’s worth. But setting that aside — I’m just totally impressed that many of these car companies are kind of going back on what they said they were going to be doing, and starting to — not reintroduce manuals, but they’re producing another extra model with the manual in it.

Barry Ritholtz (00:42:15): At a very high price. At a very high price. You look at the Porsche S/T, or all the GT3s, if you want a manual. My GTS was the last year it came with a manual, which was ’24. And the Turbo — I think 2013 was the last year with a manual, something like that. So it’s amazing — they took the supply away and said, all right, if you want a manual, we’ll give it to you, but it’s $300,000.

McKeel Hagerty (00:42:46): Yes, yes. And what they saw — they were looking at the auction data, from our auction companies and others, and suddenly the manual version of something: huge, absolute premium.

Barry Ritholtz (00:42:55): And now manual swaps are showing up in V12 Aston Martins and 430 Ferraris. I see these all the time.

McKeel Hagerty (00:43:08): Absolutely. So again, I think it’s the return of the analog — people more interested in driving. I mean, I think we’re all trying to absorb what COVID did. COVID was a boom —

Barry Ritholtz (00:43:20): I’m sure.

McKeel Hagerty (00:43:20): — time for these kinds of cars. But even afterwards, I think people were embracing slower hobbies, slower things: playing music, camping, hiking, outdoor pursuits. And in some of these things, cars sort of fit into that a little bit. Something to just go out and take a long, slow Sunday afternoon drive is not something from the rush-rush world of what mileage does it get and what’s the lease payment on it. It just comes from a different place, and there’s a bigger audience than people think who are willing to spend real money on it.

Barry Ritholtz (00:43:59): There’s a data point you guys have referenced that I want to ask you about. Quote: “We estimate that approximately 12 million enthusiast vehicles will transfer to a new generation in the United States over the next 15 years, either via estate plans or inheritances.” What is this generational handoff — from, I guess we could call them boomer collectors, to millennials and Gen Z — what does this mean for the car collecting community?

McKeel Hagerty (00:44:31): Well, I think we’ve all read that there’s this huge, gigantic wealth transfer, whatever the headline number is. I’ve heard —

Barry Ritholtz (00:44:37): 65 trillion.

McKeel Hagerty (00:44:38): I’ve heard a hundred trillion, 70. And our estimate, just on that number of 12, 13 million vehicles, is about $570 billion worth of car value right now. Most of those are held in the hands of the generation of baby boomers. I’m an older Gen Xer — Gen Xers are starting to come into their peak wealth years, past peak earnings, buying a lot of cars. But 15 years from now, about a third of that whole market will come loose. And again, we’re seeing this. Certainly the entry points are different than they were a generation ago — people are interested in sporty cars, trucks, younger kind of “youngtimer” cars, as they refer to them in Europe. We’re seeing the data. We want to position ourselves well to see that the transfers are kind of smooth, where you’re kind of helping the next generation get into these cars. We’re actually doing things like teaching manual driving classes — because it’s not just an anti-theft device, or some slow hobby like brewing beer or whatever it is. We need to teach the next generation how to drive manuals. And it’s not that hard to do it.

Barry Ritholtz (00:45:58): Not only is it not that hard, it’s just so much more engaging. And not to be a stick snob, but it really is a very different experience. And yeah, I know the GT3 in the PDK is faster than the stick — but how often am I taking my car on a track? If that’s once or twice a year, it’s a lot. What about the other 360 days a year?

McKeel Hagerty (00:46:24): Well, and even if you did — you and I, neither of us are good enough drivers to really make a difference.

Barry Ritholtz (00:46:30): Speak for yourself, McKeel!

McKeel Hagerty (00:46:31): Okay, one second — different than the laptop.

Barry Ritholtz (00:46:35): Whatever it is. It’s funny, because I’ve done all the high-performance driving classes, and the reality is, if you’re in a Roush Mustang up at Lime Rock, they said: put it into third, leave it there for the whole track. (Right, right.) So really, driving the stick isn’t that much different. But if you’re really doing a competitive course, of course not. First of all, the car doesn’t stop — the dual clutch is so fast, the engine is always engaged. (Yes.) So you’re not losing that tenth of a second when the clutch is down and you’re losing power. But it still just feels so much more engaging.

Related question to the analog and the manual: you do a Bull Market List every year — the 2025 Bull Market List. The average model year of featured cars used to be in the late eighties, early nineties. All of a sudden, it’s 2001. How did that happen? What’s driving that shift in bull market attractiveness? Is it that pre-screen, analog, manual feel — but not quite as old as the seventies, eighties cars?

McKeel Hagerty (00:47:52): I think so. But it’s also a combination of what’s driving demand. One, there’s absolutely a new cohort of people getting in, making a little bit of money, buying these things. At the top end of the market, though, it’s not just — oh, the new young tech guy who’s going to be in the OpenAI IPO and is going to make money and go buy a car. Older-generation collectors are also buying a lot of these new cars at auction. And it’s interesting — I’ve seen this twice in my career. In the big muscle car era, which was 2005, ’06, ’07, right before the great financial crisis, everybody said, oh, it’s a new generation of people buying all these American muscle cars and paying a lot of money for them. And that was true. But it was also the older generation of collectors, who liked earlier cars, saying — well, maybe those are cool and I want one too. And by the way, I have more money than you, so I’m going to outbid you at auction, and it’s mine.

Same thing right now in this, let’s say, supercar segment, where a lot of these cars from the nineties and two-thousands — we see these values going up. It is the newer money, newer collector. But it’s also an older generation of collectors saying, well, I don’t want to be left without a cool car. In fact, one guy told me recently — he bought a Bugatti Veyron and a couple of newer cars — he said, well, I want to have a car that my grandkids think is cool. And so I’m like — got it.

Barry Ritholtz (00:49:15): And that’s not the Bugatti Veyron?

McKeel Hagerty (00:49:18): Grandkids don’t like that? He says he loves it. He said, I’m taking my grandkids for rides in the Bugatti Veyron. And so they think it’s cool.

Barry Ritholtz (00:49:25): Yeah, I can imagine. Alright, last question before I get to my favorites, because I know (Yep.) we’re watching the time. So you guys crunch so many numbers, so much data. What do you think the casual observer of collector cars misses that your data is revealing?

McKeel Hagerty (00:49:44): Well, I think those big headline cars attract so much attention, and people just think it’s this crazy, very high-end market of very, very rarefied cars. And while that is true — those are the headline-grabbing numbers — the big story is that there’s just a much, much wider opportunity for people who want to play in this space. Every single price point, every little bit of reliability, and everything from pickup trucks — like I said, if you live in that part of the world and that’s something that’s interesting to you. It’s a very broad-based hobby.

It’s also — this was a hobby that for many, many years was very much male-oriented, male-driven. And I can see that in the data of who our insureds are and everything else. There’s a really rising cohort of young women — women who want to have these cars and have it be part of their lives too. I think that’s probably one of the most exciting trends. So: very broad-based.

Barry Ritholtz (00:50:43): I’ve noticed a lot more women YouTubers talking about cars.

McKeel Hagerty (00:50:47): And coming to cars and coffee with their cars, and that sort of thing. So there’s just a lot more to it. It’s much broader-based. And sure, it’s fun to see a multimillion-dollar whatever sell someplace, but that’s just not the average reality. The average is actually much broader-based and much more interesting.

Barry Ritholtz (00:51:04): So I want to get to our favorite questions, but I’ve got to throw some other stuff first. Let’s just do a quick speed round. Someone comes up to you and says: hey, I’m interested in a fun weekend car. I don’t have a lot of money, but I’d like a convertible, stick shift. What do you say?

McKeel Hagerty (00:51:19): Mustang.

Barry Ritholtz (00:51:22): Mustang, of course. Other than a Ferrari, you say “of course” — because I would’ve said Miata.

McKeel Hagerty (00:51:26): Oh yeah. Well, Mustang or Miata. And I always tell people — the oldest Miata is now 33 years old, something like that. And they made over a million of them for the US market. Super reliable. If you want to go track driving, they’re the great track cars. If you want to just cruise around on a weekend, they’re inexpensive — 10, 15 thousand dollars. (Right.) But same thing with the Mustang.

Barry Ritholtz (00:51:49): And a little more horsepower in the Mustang.

McKeel Hagerty (00:51:51): A little bit more horsepower. They made a lot of convertibles. They’re manuals — they’re automatics, if you don’t feel comfortable with that. And very, very affordable cars, and easy to get serviced. So those would be my two recommendations. Of course, the most collected car, though, still in the United States is the Corvette. They’ve been making them forever. There are lots of them. Easy to service.

Barry Ritholtz (00:52:13): And not that expensive — especially like a C6 or C7. Not for a semi-modern car.

McKeel Hagerty (00:52:19): They’re amazing. They’re amazing cars.

Barry Ritholtz (00:52:22): Someone says, I’m interested in something European, a little more interesting, sporty. Where do you send them?

McKeel Hagerty (00:52:29): Well, I’m a Porsche person, so I would say: great, you want a 911, but let’s start you in a Boxster — some more entry point there. And that younger generation that I talked about — the 3 Series BMWs: super fun cars, lots of them built, with a lot of quality, and they kind of have style. They look good. That’s where people go.

Barry Ritholtz (00:52:53): Yeah, those have aged beautifully — the design of the early BMWs. Someone who has a little more scratch, a little older, says: hey, I’m looking for something fun, but it’s going to retain its value, and I’m willing to spend more than my kid buying a Boxster.

McKeel Hagerty (00:53:12): Well then — again, my bias here — I’d still probably say 911, but you’re going to pick a year that was maybe slightly off. They’re going to hold their value well. I actually did a kind of market-cap comparison between every 911 ever built versus every Ferrari ever built. Because people talk about Ferrari GTOs and all this sort of thing, which are worth tens of millions, but I’m like —

Barry Ritholtz (00:53:36): 275s. Yeah. And they were just spectacular.

McKeel Hagerty (00:53:39): They are. I love them. But when you look at all the 911s that were built — they were really undervalued for a long time. I mean, people used to give me a hard time, because my ’67 911S — when I spent over a hundred thousand dollars having it professionally restored, not that many years ago — I mean, after my very amateurish high school restoration — I spent a hundred thousand, or a little bit more than that, and it was worth about 70. (Right.) Well, now it’s worth about 300. (No kidding.) Yes — 250, 300 for a ’67 S. And people say, what’s your 911 worth? I’m like, I don’t care. It’s my baby. I and my family will have that car forever.

Barry Ritholtz (00:54:22): I have a bias against garage queens, but I’m curious as to your thoughts — people who buy cars, put them in a garage, never drive them.

McKeel Hagerty (00:54:30): I think those are really sad cars.

Barry Ritholtz (00:54:32): Right? They’ve got to be great for business, because there’s zero risk.

McKeel Hagerty (00:54:35): Yeah, the claims are low. But they’re sad cars. And especially — by the way, there’s almost not a single generation of cars that fares well when it sits around for a long, long period of time. Tires age, belts and hoses age. And some of those nineties and two-thousands cars, they age particularly badly when they sit in the garage. Lots of maintenance required. So my view is — if you’ve got a car, unless it’s got six miles on it, or 15 miles, and you just think that’s what makes it cool (and there are a lot of customers that we have that like that), my view is: go drive it. We sold at our Amelia sale one of the two record-setting Ferrari Enzos. We sold it for $15 million. The car had, I think, 249 miles on it. A Ferrari Enzo. And everybody’s like, what do you think of that? I’m like — I would rather have the 20,000-mile Ferrari Enzo that I could go drive. I mean, that’s just personally myself. And I congratulated the buyer — wonderful buy, sir. But I would like the —

Barry Ritholtz (00:55:30): Please drive it. Please drive it. Doug DeMuro said something really interesting about his Carrera GT. When he was hunting for one, he found one with higher mileage, because he said: I won’t go through the process of “I’m not going to drive this because I’m depreciating it.” Starting out higher mileage, you’re more inclined to put miles on it.

McKeel Hagerty (00:55:50): I have one vintage car that has super low miles on it. It’s a Jaguar E-Type, 1966. (Lovely.) It had 13,000 miles on it when I bought it, and it has about 15,000 miles on it now. And it just bugs me, because I feel like it should be driven — and then I worry that I’m just putting a bunch of miles on it. So I don’t know — I have the same quandary. So I just like to drive cars.

Barry Ritholtz (00:56:11): So we are recording this right after Ferrari dropped their new Elettrica — electric appliance, I don’t even want to call it. My Ferrari buddies are not big fans of all the new versions that have been coming out. I still think the 458 is really handsome. I love the 812 GTS — if I ever get that garage built, one of those has my name on it. But the question for you is: when you see these new cars coming out, and they’re so technology-heavy and so screen-focused, how do you think these will fare as collectibles 20, 40, 60 years from now?

McKeel Hagerty (00:57:01): Well, I can tell you, I will never bet against Ferrari. Not ever once. Because it is just — forever, since the day the first one was built, there’s been something magical about that brand. I love the history — the fact that when Enzo Ferrari, back in the day, would show up with one, everybody knew: well, that’s the car to beat, period. And even though sometimes you beat them, sometimes you didn’t, they were just the car to beat. And I also remind people that companies like Ferrari have always had different lines of cars. Ferrari always had race cars, but they also always had their, like, businessman’s car — a front-engine, slightly less performance —

Barry Ritholtz (00:57:40): The 550s, 599s, 612s. Exactly. Even the 575.

McKeel Hagerty (00:57:44): Well, and the SUV — the Purosangue, right? People said they’ll never build an SUV. And I remember I was talking to Bob Lutz, and he just said: watch. I’m like, why do you think they will build an SUV, Bob? And he said: because they have to.

Barry Ritholtz (00:57:58): I was going to say — the Cayenne and the Macan saved Porsche.

McKeel Hagerty (00:58:02): They saved Porsche.

Barry Ritholtz (00:58:03): All right. (Yes.) Ferrari had to be watching that. They had to be seeing the Urus sales. (Yes.) Which is essentially a rebadged truck from Audi with a whole lot more horsepower. I mean, how do they not do that?

McKeel Hagerty (00:58:18): They had to. And I think — I get it. This particular electric car has not necessarily had the most favorable initial reviews. But my view is, I will never count Ferrari out. And I think they probably are seeing some things in their data, and with some certain customers who want this. And we’ll see.

Barry Ritholtz (00:58:34): We’ll certainly see. So let me jump to my favorite questions (You bet.) so I don’t make you late for your trip back to the Midwest. Who were your early mentors who helped shape your career?

McKeel Hagerty (00:58:48): My mentors went from kind of macro mentors to micro mentors. In the early days, of course, it was my parents. My parents had very different skill sets, and I was so blessed that I got to work with both of them. There were some teachers early on who were really extraordinary professors, who I think triggered my love of learning. One gentleman — his name was Gary Hart, still living; I kind of look after him in his old age — he just fundamentally taught me how to be a good student.

But what I found, though, is my mentors have become more micro mentors now. Less of — it’s my whole life, learning everything about something from this person. Now I find somebody who’s really good at one thing, and I learn from them. I become friends with them. My current lead director on our public company board, Bill Swanson — he was the chairman and CEO of Raytheon. Wonderful man, car collector, and just brilliant at board governance and how to think things through. And I’m just learning so much listening to him. And so he is a real mentor of mine. And so I think I’m very much of that tribe-of-mentors approach. I’ve had many, and I love mentoring myself.

Barry Ritholtz (00:59:58): Huh — really, really interesting answer. What are some of your favorite books? What are you reading right now?

McKeel Hagerty (01:00:02): So I’m an avid reader. I read 30 to 50 books a year, typically. (Wow.) And a lot of biographies. In the last four or five years, I was definitely on a music biographies stint — so, a lot of rock and roll biographies.

Barry Ritholtz (01:00:17): Give us a few names.

McKeel Hagerty (01:00:18): Oh, everything from the Keith Richards to Slash to — you name it. I read a lot of biographies: Springsteen, anybody. Then I did an interesting kind of parallel set, which was music producers. And that was fun. So everything from — there’s a famous book on Warner Brothers music called Sonic Boom, which was about all of the music producers that did that — to Clive Davis, to those types of folks.

For this year, though, my reading theme is all about the founding of America. So I’m reading a lot of kind of American founding stuff — I just figured it’s a good time to do that. (Sure.) So, biographies so far this year on George Washington, Benjamin Franklin; there were a bunch of other books around a lot of the founding fathers. I’m also wading through Wealth of Nations again, for the first time since college — because it was also published in 1776. I’d forgotten that.

Barry Ritholtz (01:01:13): That’s a little bit of a slog.

McKeel Hagerty (01:01:14): Yeah, that’s a beast. That’s a beast. But I would say one final piece — I was a sci-fi fan forever. (Oh really? Same.) And I decided, for the last two years, to start rereading a bunch of the great series that I read a long time ago. So I just read the entire Dune series for the third time in my life. (Wow.) And that was fun. The Foundation series, all of Clarke. I think what I had forgotten is that almost all of those sci-fi authors knew each other. (Yes.) They all kind of subscribed to some of the same magazines, and they’d get together for these little get-togethers, and they were all kind of envisioning a future together. And a lot of the same themes — and especially right now, the challenges with AI — are all embedded behind the Foundation series, and even in Dune. You kind of have to read into it, but it’s fascinating stuff.

Barry Ritholtz (01:02:08): Larry Niven, Philip K. Dick — any of those?

McKeel Hagerty (01:02:12): Yes. And of course, Hitchhiker’s Guide to the Galaxy — for a little bit of humor.

Barry Ritholtz (01:02:17): Classic. Yes. What are you streaming these days? Give us your favorites — either YouTube or Netflix, or even podcasts. What’s keeping you engaged?

McKeel Hagerty (01:02:25): Yeah — so my workout companion is a lot of podcasts. And they’ve kind of shifted, I guess, a little bit. During COVID, it was a lot of sort of habits-and-mindset stuff and that sort of thing. And then I discovered people like Scott Galloway — his very humorous way (Sure.) to think about business. Tyler Cowen, I think, is just absolutely brilliant — so, great podcast there. I’ve also been impressed with — Audible has a number of their own. Again, back to the musical biography thing — they have a lot of these short-format podcasts, kind of quasi-musical performances that are both kind of spoken word and music in one. It’s actually called the Words and Music series. And that’s been really fun to listen to some of those.

Barry Ritholtz (01:03:13): Words and Music. Yes — I’m going to have to check that out. All right, our final two questions. What sort of advice would you give a recent college grad interested in a career in either automobiles or insurance, or business?

McKeel Hagerty (01:03:27): I’ve just been to two different commencement ceremonies. One was my daughter’s, and another was some friends’. And all of the commencement speakers right now are so focused on AI, and trying to tell them it’s going to be okay. And not only do I think it’s going to be okay — as I always remind them, and people, of my own career: my core business is what some people would call a relatively boring industry, insurance. You don’t have to go into the cool stuff. I think there are so many opportunities in these industries that are established, they’re stable, and they need really smart people who want to work hard and remake what they are. So don’t overlook things that you consider boring today. Look at some of those, and think about the types of people that are going into them, where you can make a great career. I never imagined I’d be doing what I am today, and I think I have the coolest job you can have.

Barry Ritholtz (01:04:23): Huh. Really, really interesting. And our final question: what do you know about the world of automobiles or insurance today that might have been useful 30, 40 years ago when you were first ramping up?

McKeel Hagerty (01:04:36): I think the world has been predicting the demise of certain parts of the automobile industry for years. And we saw it very recently with this almost, like, holy war of how people view the difference between EVs and internal-combustion cars. And I’m very agnostic about all of that stuff. And it’s very easy to kind of get sucked into those arguments — like, well, what do you think of EVs? I’m like, I don’t know. There were EVs back in 1908. (That’s right.) There were steam cars in 1910. And now, you know, we’ve been on internal combustion for a long time. I think there will be more electric cars in the future, but I also think there are going to be great internal-combustion cars. So I think I would just continue playing the big long game, and don’t worry about some of the little petty arguments that people can have. It makes for good cocktail party talk, maybe, but I’d like to see the big picture.

Barry Ritholtz (01:05:29): McKeel, thank you for being so generous with your time. We have been speaking with McKeel Hagerty, chairman and CEO of Hagerty specialty insurance. If you enjoy this conversation, well, be sure and check out any of the 648 we’ve done previously. You can find those at YouTube, Apple, Spotify, Bloomberg — wherever you get your favorite podcasts.

I would be remiss if I didn’t thank the crack team that helps us put these conversations together each week. Alexis Noriega is my video producer. Sean Russo is my researcher. Anna Luke is my podcast producer. I’m Barry Ritholtz. You’ve been listening to Masters in Business on Bloomberg Radio.

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The post Transcript: McKeel Hagerty, CEO and Chairman of Hagerty Insurance appeared first on The Big Picture.

• Gold’s Faithful Think Twice as Prices Slide From Record Highs: The metal declined again Monday after the U.S. and Iran traded a fresh round of attacks. Gold slides off record highs and the faithful are wobbling. Nothing tests conviction quite like a drawdown. After the U.S. and Iran traded a fresh round of attacks, gold took yet another dip Monday (Wall Street Journal)

• Returns to “Do-Nothing” Portfolios. Hendrik Bessembinder studies outcomes for a variety of “do-nothing” portfolios constructed from constituents of the S&P 500 index, from 1971 to 2025. These portfolios maintain their positions even for those stocks that exit the index. The findings include (i) initially equal-weighted portfolios outperform initially value-weighted portfolios over the full sample period, (ii) value-weighted “do-nothing” portfolios essentially match the index on average… New SSRN research on ‘do-nothing’ portfolios: buy, hold, resist the urge to fiddle. Sloth as alpha — my kind of strategy. (SSRN) see also Strategy: The AI Arms Race. Starting in the mid 1990s, the US and China embarked on radically different but complementary paths that led to a sharp growth divergence with other advanced economies, most notably, Europe and Japan. US innovation focused on the value layer of the digital economy, including internet platforms, software, semiconductors and cloud. China, by comparison, focused on the infrastructure and manufacturing layers of the physical economy, climbing the value chain over time with technology innovation. (MUFG)

• The World Is Cutting Ties With America. It’s Already Costing Us.: The world is quietly rerouting trade, alliances, and trust around America — and the bill is already arriving. (New York Times)

• Why Are Berries Everywhere, in Every Season? Driscoll’s.: The NYT on the company that engineered year-round berry availability — and what that triumph of supply chain management means for agriculture, flavor, and the way we eat. (New York Times)

• States with the most—and least—housing market inventory: heading into the core summer season National active housing market inventory growth is at a crawl—but not in Washington. The geographic divergence in housing inventory is dramatic. Some markets are flooded; others are still bone-dry. Fast Company maps where buyers have leverage and where they don’t. (Fast Company)

• A Robot Army Remakes Ground Warfare in Ukraine: They began as supply mules. Now ground robots evacuate the wounded, hold trenches and even do the killing. Ground robots are remaking warfare in Ukraine — the drone war has officially come down to earth. (New York Times) see also See How Ukraine Is Taking Out Russia’s Refineries: Ukraine is targeting Russian energy infrastructure with its growing fleet of long-range drones and missiles, causing fuel shortages in one of the world’s biggest oil and gas producers and embarrassing President Vladimir Putin. The long-range strikes on Russia win rare praise for Ukraine from Trump. The Journal’s visual dive into Ukraine’s campaign against Russia’s refineries — degrading Moscow’s war economy one strike at a time. Long-range strikes unleash fuel crisis in Russia and win rare praise for Ukraine from Trump (Wall Street Journal)

• Some Monsters are Real: What’s coming has never been seen before in the history of modern global industrial civilization … and it’s just getting started. Climate Casino on the extreme weather events that used to be theoretical and are now showing up in the data with alarming frequency. The tail risks aren’t in the tail anymore. (Climate Casino)

• Lindsey Graham sacrificed his reputation to Donald Trump. He got plenty in return. His career explains why so many Republicans made peace with Trump — and what they gave up to do it. His career explains why so many Republicans made peace with Trump — and what they gave up to do it. (Vox)

• 50 Parting Thoughts From 2026 Wimbledon: Jon Wertheim’s annual tradition: 50 parting thoughts from Wimbledon — the champions, the chokes, and everything in between. (Sports Illustrated)

• The Hydration-Break World Cup: It is axiomatic that countries hosting the World Cup try to put their best face forward. During the monthlong tournament, streets are cleared of anything (and anyone) that might offend the eye, political evils are swept under the rug, warm welcomes generally abound, and even authoritarian states, or those with notoriously disturbing human rights records, present themselves as sporting, full of bonhomie, and as cuddly as their official stuffed mascots. This time around, Mexico and Canada appear to have offered the standard warm embrace to teams and tourists alike; Mexico went so far as to provide a base for the Iranian team after the U.S. refused to allow its members to train, or even stay overnight, on American soil.. Jonathan Wilson on the hydration-break World Cup — soccer in the age of extreme heat, where the beautiful game melts. (The Paris Review)

Video of the day: How America Turned The Dollar Into A Weapon:

Be sure to check out our Masters in Business interview this weekend with McKeel Hagerty, CEO and Chairman of Hagerty. We discuss how he transformed the family boat insurance business into a “sexy” driver-forward business. We also discuss our love of collectable cars and his love of his first car, a Porsche, that he bought at the age of 13.

Only two names from the Dow Jones Industrial Average of July 1976 remain today. Many of today’s tech Blue Chips didn’t even exist then.

Source: Barron’s

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• War Leaves Economy With More Stubborn Inflation, In latest Journal survey, economists have lowered the probability of recession but see inflation staying higher longer. The Iran conflict is embedding higher costs into the economy in ways that won’t reverse when the fighting stops. Economists are raising their inflation forecasts for 2027 and beyond. (Wall Street Journal)

• Oh, the Stories the Dow Can Tell. Lessons From the Index’s Past 50 Years. Only two names from the Dow Jones Industrial Average of July 1976 remain today. Many of today’s tech Blue Chips didn’t even exist then. (Barron’s)

• All you never wanted to know about corporate bond market issuance: How the debt capital markets sausage gets made. FT Alphaville’s deep dive into the plumbing of corporate bond markets—the mechanics, the distortions, and the risks hiding in plain sight. (FT)

• The Economics of Friendship: Why does loneliness seem to be on the rise? In part because we’ve made life frictionless and efficient. The Wall Street Journal opinion page goes long on something economists rarely study — the measurable economic value of having close friends. Social capital isn’t a metaphor; it shows up in earnings, health outcomes, and longevity data. (Wall Street Journal)

• Publishers Are Preparing to Opt Out of Google Search: After years of giving away content for free traffic, major publishers are seriously considering pulling the plug on Google indexing entirely. The economics of search have finally broken. (Adweek)

• The first American autonomous ground vehicles are fighting in Ukraine: Forterra, a U.S. builder of autonomous vehicles, revealed today that more than 100 of its self-driving ATVs have been deployed in conflict zones in Ukraine for the past nine months, in what the company believes is the largest deployment of autonomous ground vehicles in combat by any U.S. defense tech company. (Techcrunch) see also Ukraine’s Killer Robots Show How War Is Changing: Autonomous weapons are no longer theoretical. Ukraine’s battlefield is the live proving ground for AI-driven combat systems that will define the next generation of warfare. (The Conversation)

• China, Russia and Others Seek to Inflame Debate Over A.I. Data Centers: State actors in China, Russia and Iran have sought to exploit the U.S. public debate over the effects of the technology.  We have seen bad overseas actors use social media to influence elections, debate of Israel, Ukraine, and now AI. America needs to wake up and recognize this credible security threat to our sovereignty and democracy. Foreign adversaries are exploiting local opposition to AI data center construction — amplifying environmental and energy concerns to slow down America’s AI infrastructure buildout. (New York Times)

• How Physicists Track and Trap the Elusive Neutrino: The hunt for these ghostly particles has required some of the most audacious experimental setups ever built. In the 1960s, Raymond Davis Jr. and colleagues at Brookhaven National Laboratory placed a tank 1.5 kilometers underground in the Homestake mine in South Dakota and filled it with nearly 400,000 liters of a chlorine-based cleaning fluid called perchloroethylene. On the rare occasion that a passing neutrino struck a chlorine nucleus, it would be transformed into a radioactive form of argon that could be detected and counted. The experiment, which would run for 25 years, found just one-third the number of neutrinos coming from the sun that had been predicted in theoretical models. (Quanta Magazine)

• The U.S. men played ‘scared.’ Fox’s Carli Lloyd was fearless in her candor.: The USMNT’s World Cup performance was underwhelming: “I felt like they lost the game before they even stepped out on the pitch,” said Lloyd, the Fox Sports analyst on the post-match show. “And I’m not sure why, and I don’t know the reasons. But just from the beginning: chasing. Tentative. Scared. Just not confident on the ball.”   (The Athletic)

• Robert De Niro Only Wants to Shoot in New York: The actor and his partners recently opened Wildflower Studios, a 775,000-square-foot production facility in Queens. The NYT real estate section catches up with De Niro’s long love affair with the city and his insistence on keeping production local. A profile that’s half cinema, half urbanism. (New York Times)

Video of the day: How America Turned The Dollar Into A Weapon

Be sure to check out our Masters in Business interview this weekend with McKeel Hagerty, CEO and Chairman of Hagerty. We discuss how he transformed the family boat insurance business into a “sexy” driver-forward business. We also discuss our love of collectable cars and his love of his first car, a Porsche, that he bought at the age of 13.

America’s missing middle: The shrinking 45-64 population

Source: Axios

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• It’s a World-Class Investment. It’s a Junk Investment. What Is Going On With SpaceX? The answer starts with Wall Street’s long-held distinction between “smart money” and “dumb money.” In that view, the roughly $2 trillion value that the stock market is affording SpaceX — about the same as Amazon’s value, and more than JPMorgan’s and ExxonMobil’s combined — is being set by naïve investors who think Elon Musk’s promises will all miraculously be realized. The debt, on the other hand, is being priced by seasoned investors, the ones who understand that profits actually have to be earned, and who are rightly skeptical of Mr. Musk’s grand pronouncements. SpaceX is simultaneously the most coveted private asset on earth and a governance nightmare. Bethany McLean on the paradox of a company that’s worth $350 billion and run like a startup with no board oversight. (New York Times)

• How Rogue Nations Are Using Cryptocurrencies to Evade Sanctions: Blacklisted entities handled $100 billion in crypto in 2025, financing terrorism and weapons. The WSJ maps the workaround economy — and it’s bigger than you think. (Wall Street Journal) see also Trump’s $1.4 billion crypto disclosure: The White House insists there’s no conflict of interest as Trump reports $1.4 billion in income from an industry he’s deregulated. Molly White digs into the president’s financial disclosure and finds the conflicts of interest are no longer theoretical — they’re on the form. (Citation Needed)

• Jessica Burbank on the Rise of Flock Safety and America’s Surveillance State. Investigative journalist Jessica Burbank explains how the company quietly won government contracts across the country—and why communities are starting to push back. Current Affairs interview on how Flock Safety’s license plate readers have quietly blanketed the country — and why most Americans have no idea how thoroughly their movements are being tracked. (Current Affairs)

• Has America Crossed the Asshole Threshold? Civilizations can carry a surprising number of parasites and live. But there’s a line — Rome crossed it, the Gilded Age toed it, and for the first time in history, we can measure it. The Grim Historian asks the title question: whether there’s a tipping point at which institutional rudeness, bad faith, and cruelty become self-reinforcing cultural defaults. (Defector)

• The End of Reading Is Here: Optimists once believed that universal literacy was inevitable. Now it seems that the age of reading might be a short anomaly in human history. The Atlantic‘s cover story on the collapse of sustained reading as a cultural practice — and what a post-literate society actually looks like. Not the death of books, but the death of the attention required to read them. (The Atlantic)

• Watchdog warns of risks to patients as private equity’s stake in US healthcare grows: New report details slew of ventures between private equity and nonprofits and calls for greater government oversight. Color me unsurprised. (The Guardian)

• The Supreme Court is corrupting American democracy: One cannot hope to bribe or twist/ (thank God!) the U.S. chief jurist. To understand this, you need to think more systematically about the relationship between democracy and corruption. The best way of understanding this relationship that I know of is laid out in an academic article that was published the year before John Roberts was named Chief Justice, Mark Warren’s “What Does Corruption Mean in a Democracy?” Henry Farrell argues the Supreme Court is corrupting American democracy — not decision by decision, but structurally. (Programmable Mutter)

• Why U.S. measles outbreaks have grown harder to extinguish: The nation is already nearing last year’s record case total, and experts say the virus is forcing doctors to relearn a disease many thought had been consigned to history. Why measles outbreaks keep getting harder to extinguish: falling vaccination rates meet a weakened public-health system. Entirely predictable, entirely preventable. (Washington Post) see also As Parents Reject Vitamin K Shots, Some Babies Develop Devastating Bleeding: Doctors described treating brain and abdominal hemorrhages in infants who hadn’t received the routine injection. Several said the images of those patients were seared in their minds. • As Parents Reject Vitamin K Shots, Some Babies Develop Devastating Bleeding: The NYT documents the real-world consequences of vaccine hesitancy’s cousin: parents declining a routine newborn treatment that prevents a rare but catastrophic bleeding disorder. (New York Times)

• Bari Weiss Is Filling CBS News With British Right Wing Propagandists: from the you’re-simply-not-very-good-at-anything dept; As we’ve long explored, Weiss wasn’t hired to do journalism. She was hired to do right wing agitprop. But given she’s not good at that either, CBS just saw its lowest ratings in a quarter century.  (Techdirt)

• How Olivia Rodrigo Is Getting Back at the Trump Administration: The pop star is turning her platform and her festival into an organizing machine. The Hollywood Reporter on her evolution from heartbreak anthems to political action. (Hollywood Reporter)

Video of the day: How Hinckley Outlived 90 Years of American Boatbuilding Disasters.

Be sure to check out our Masters in Business interview this weekend with McKeel Hagerty, CEO and Chairman of Hagerty. We discuss how he transformed the family boat insurance business into a “sexy” driver-forward business. We also discuss our love of collectable cars and his love of his first car, a Porsche, that he bought at the age of 13.

Americans are set to lose nearly $250B gambling this year—a record high, up more than 60% since 2019—and that’s before counting unofficial betting via prediction markets or crypto

Source: Joseph Politano

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To learn how these reads are assembled each day, please see this.

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This week, I speak with McKeel Hagerty, CEO and Chairman of Hagerty. We discuss how he transformed the family boat insurance business into a “sexy” driver-forward business. We also discuss our love of collectable cars and his love of his first car, a Porsche, that he bought at the age of 13.

A transcript of our conversation is available here on Tuesday; A list of his current reading is below.

You can stream and download our full conversation, including any podcast extras, on Apple Podcasts, Spotify, YouTube (video), YouTube (audio), and Bloomberg. All of our earlier podcasts on your favorite pod hosts can be found here.

Be sure to check out our Masters in Business next week with Jason Wenk, founder and CEO of Altruist, a modern custodian built as a clean sheet from the ground up, fully integrated with artificial intelligence. He began his career at Morgan Stanley before launching Retirement Wealth Advisors, and then FormulaFolios. The through-line of his career has been creating lower-cost, tech-enabled, financial advice.

Current Reading/Favorite Books

Lots of musical bios:  Keith Richards, Slash others
Hitchhiker’s Guide to the Galaxy
Sonic Boom
George Washington
Benjamin Franklin
Wealth of Nations
entire Dune series
The Foundation series,

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• The Anti-Amazon. One brilliant feature of the Costco experience is, paradoxically, the constraint: as opposed to Amazon, with its near infinite assortment, or even Walmart, which has approximately 130,000 SKUs (stock keeping units, or distinct items) in the average Supercenter, any given Costco will only hold 4,000 SKUs to choose from. While most retailers today assume that consumers want ever greater assortment, Costco’s popularity speaks to a countervailing desire for less choice. Indeed, the pre-selection of items for sale in their warehouses is part of the value proposition: not only are you going to get a lot of a particular thing for a good price, but you also won’t have to deliberate over micro-differences in a more robust assortment. Benjamin Fong on what a genuine alternative to Amazon’s logistics empire would require. A serious, wonky look past the everything-store. (Phenomenal World)

• How do you solve a problem like social media? Part I It’s all well and good saying we should regulate social media. But social media is already regulated. So why is it failing? And what could we do in response? The first installment of a serious policy analysis of what regulation would actually look like—beyond the usual hand-wringing and congressional hearings that go nowhere. (Chaminda Jayanetti) see also At 17, She Sued Meta and Google, and Won. Now She’s Ready to Tell Her Story: Kaley Glenn-Mills’ lawsuit reshaped the fight to protect children from social media. She says she still can’t stop scrolling. . (Bloomberg free)

• The Second Derivative: Why No One Understands the AI Boom: The market misremembers 2008. That same blind spot sits at the center of the AI boom. The second derivative problem: bulls and bears alike are arguing about the AI boom’s level when the rate of change is what matters. (Groundbrkr)

• ‘There Is No Going Back’: The Inside Story of Europe’s Rupture With America: Trump’s tariffs, threats against Greenland spurred a rebellion by top leaders; the limits of ‘flattery diplomacy’. The WSJ’s inside story of Europe’s rupture with America: “There is no going back.” The post-war alliance, unwinding in real time. (Wall Street Journal) see also The Canadian Who Steered Europe Away From the U.S. Facing threats from Trump, Mark Carney emerged as a central figure in a project to reshape the Western alliance The WSJ profiles the diplomat who helped Europe decouple from American strategic dependence — a realignment that will outlast any single administration. (Wall Street Journal)

• The Great Blogging Collapse: What Happened to 100 Successful Blogs? [Study] I tracked 100 once-successful blogs over four years to understand what happened after Google’s Helpful Content Updates and the rise of AI Overviews. The results were striking: the median blog lost 85% of its organic traffic, while only 21 continued to grow. This study reveals the patterns behind the winners, the losers, and what it takes to build a blog that can survive in 2026.(Daniel Stanica)

• What Makes Humans Stupid: It takes intelligence to get things spectacularly wrong. An essay on our undoing. Nautilus on the cognitive biases, social pressures, and structural incentives that systematically produce bad decisions—even among the smartest people. (Nautilus)

• Capitalists Love This Podcast. So Do Their Critics. “Odd Lots” goes deep on lentils in Saskatchewan, the global tractor supply and trucking markets. Is it the skeleton key to understanding this strange economic moment? Congrats to Jope & Tracey!  The NYT profiles Odd Lots, the Bloomberg podcast that’s become required listening for both the financial establishment and the people who want to dismantle it. The rare show that doesn’t condescend to either audience. (New York Times)

• The Inside Story Of Leverage Research 1.0 Between 2011-2019, Leverage Research explored the deep psychology of Effective Altruism and Silicon Valley, then suddenly dissolved among rumors of “demons.” What happened? Lydia Laurenson’s firsthand account of Leverage Research 1.0 — one of the rationalist movement’s stranger experiments, told from the inside. (Substack)

• The Terrorist in the Brain: What Robin Williams and Bruce Willis can teach us about dementia—and about the industry that has grown up around our fear of it Skeptic on Lewy body dementia — the ‘terrorist in the brain’ that claimed Robin Williams and afflicts Bruce Willis — and what medicine can actually offer. (Skeptic)

• How Lizzo Became One of Pop Culture’s Great Flops: The singer is experiencing a new form of downward mobility—and she’s not alone. The Atlantic on how Lizzo became one of pop culture’s great flops — a case study in how fast fame’s flywheel reverses. (The Atlantic)

Video of the day: Every Jon Favreau Movie, Explained by Jon Favreau | Vanity Fair

Be sure to check out our bonus episode of Master’s in Business with David Risher, CEO of Lyft, one of North America’s largest ride-sharing networks. He joined Lyft’s board in 2021 when the firm was burning cash and losing ground to Uber. Lyft has returned to profitability, with its stock rising more than 75% since Risher took the reins as CEO in 2023. In Q1 2026, the firm had 28.3 million active riders and did $4.9B in gross bookings, with $1.7B revs, and $132.8m in EBITDA. Previously, he held senior roles at Microsoft and Amazon.

Mag-7 underperformance returns top 5 S&P 500 weighting to the level 2 years ago

Source: Deutsche Bank Research Institute

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• Europe chose insurance. America chose growth. Europe and America chose different points on the efficiency-equity trade-off. That used to be a matter of preferences. It isn’t anymore. Visitors notice something else, even the ones who have never heard of a purchasing power parity adjustment for GDP per capita comparisons across borders. They notice the wealth. The cars, the houses, the restaurants, the sheer scale of consumption. They notice the contrast between what is happening here and what is happening back home. You don’t need the IMF’s World Economic Outlook to see it, though the WEO will confirm it: even after adjusting for purchasing power, U.S. GDP per capita is now roughly 38% higher than the EU average. (The Two Cents)

• Boomers’ massive wealth will mostly be passed down to people who are already rich: Baby boomers are expected to pass $36 trillion to their heirs in the next two decades, an analysis found. The great wealth transfer is coming — and it’s going exactly where you’d expect. The Washington Post on the data showing intergenerational wealth concentration accelerating, not dissipating. (Washington Post) but see Hey … can you pay me back now? Welcome to the summer of financed fun, where one friend books the Airbnb and everyone else promises the money is coming. The psychology of the awkward IOU — why asking friends to pay you back is one of money’s great social minefields. (Substack)

• The Insider’s Guide to San Francisco’s A.I. Boom: The city is the tech industry’s hub for artificial intelligence, 30 miles north of the home of companies like Meta and Google. What if San Francisco is the new Silicon Valley? San Francisco has had its share of tech companies since the dot-com boom, but the money pouring into artificial intelligence has lately supercharged the city’s tech profile.
Last year, they raised nearly $35 billion of venture capital funding. The change is visible. Rents are climbing again. City buses are filling back up. And the face of San Francisco is starting to look younger. The NYT maps the geography, social dynamics, and power structures of SF’s AI scene. Where the money is, where the talent eats, and who’s actually building things versus just talking about them. (New York Times)

• The Fun Shortage Is Real, and It’s Making America Miserable: With fewer places to relax and socialize, and steeper prices for entry, having fun is quantifiably harder than it used to be. Bloomberg on the fun shortage: hotels, theme parks, and summer camps priced past the middle class. Even leisure is bifurcating. (Bloomberg free)

• The creator economy is above the law: How influencers get away with anything. the Polymarket campaign was definitely illegal. However, there’s a reason that Polymarket and most content creators don’t abide by these laws: They’re barely being enforced. Scott Galloway’s shop argues the creator economy operates in a regulatory vacuum. Influence without accountability rarely ends well. (ProfG Media)

• The year is 2063 and you were never interesting. You’re never going to be someone’s eccentric grandmother because you spent your best years consuming the lives of strangers. A sharp bit of speculative fiction: the year is 2063 and you were never interesting. The algorithm always knew. (Substack)

• Navigating by Aliveness: One thing that’s missing from those discussions is any consideration of aliveness. Yet I think it might be the key to understanding how to think and feel about AI, how to respond to it, how to integrate it into our lives or not – and how to ensure, as technology marches on, that we don’t lose sight of what really matters for a meaningfully productive life. Oliver Burkeman on navigating by ‘aliveness’ rather than obligation — his usual gentle antidote to productivity culture. (Oliver Burkeman)

• The last astronomers: Amid a flood of AI advances, astrophysicists are questioning the soul of their field. (Science)

• The only bias uncovered in the White House’s Smithsonian report is its own: A White House report alleges radical bias at the National Museum of American History. But the assembled evidence reveals a large and vibrant institution carrying out its mission. A pointed WaPo column: the only bias uncovered in the White House’s Smithsonian report is its own. (Washington Post) see also A Huge Escalation in Trump’s Smithsonian Meddling: A White House report details what the administration wants to change in museums—and suggests that a crackdown could be coming. The Atlantic on a huge escalation in Trump’s Smithsonian meddling — the American History museum is now squarely in the crosshairs. (The Atlantic)

• The Wimbledon boy living a dream that defies belief: If it were a movie script, Arthur Fery’s remarkable Wimbledon adventure would probably never have made it to the big screen because it seemed ​too far-fetched to be believable. A 23-year-old who grew up within walking distance of Centre Court. Ranked 114th in the world. A wildcard ‌entrant with only two previous Grand Slam match wins. Wimbledon semi-finalist? Reuters’ profile of the young tennis sensation whose run at the Championships is the feel-good sports story of the summer. (Reuters)

Video of the day: Why The Best Player Alive Barely Runs

Be sure to check out our bonus episode of Master’s in Business with David Risher, CEO of Lyft, one of North America’s largest ride-sharing networks. He joined Lyft’s board in 2021 when the firm was burning cash and losing ground to Uber. Lyft has returned to profitability, with its stock rising more than 75% since Risher took the reins as CEO in 2023. In Q1 2026, the firm had 28.3 million active riders and did $4.9B in gross bookings, with $1.7B revs, and $132.8m in EBITDA. Previously, he held senior roles at Microsoft and Amazon.

Percent Change in Median House Prices from 2000 to 2025 in the US

Source: Data is Beautiful

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